AT299244B - Process for the production of new organotin compounds - Google Patents
Process for the production of new organotin compoundsInfo
- Publication number
- AT299244B AT299244B AT1043470A AT1043470A AT299244B AT 299244 B AT299244 B AT 299244B AT 1043470 A AT1043470 A AT 1043470A AT 1043470 A AT1043470 A AT 1043470A AT 299244 B AT299244 B AT 299244B
- Authority
- AT
- Austria
- Prior art keywords
- general formula
- organotin compounds
- production
- tin
- new
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PQDMBPWHACLCQH-UHFFFAOYSA-M 3,5-dichloro-2-tributylstannyloxybenzonitrile Chemical compound C(CCC)[Sn](OC1=C(C=C(C=C1Cl)Cl)C#N)(CCCC)CCCC PQDMBPWHACLCQH-UHFFFAOYSA-M 0.000 description 1
- LIYBDCPQHBTRQU-UHFFFAOYSA-M 5-chloro-2-tributylstannyloxybenzonitrile Chemical compound C(CCC)[Sn](OC1=C(C=C(C=C1)Cl)C#N)(CCCC)CCCC LIYBDCPQHBTRQU-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Organozinnverbindungen
Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Organozinnverbindungen der allge- meinen Formel
EMI1.1
worin Rein Alkylrest mit 4 bis 8 C-Atomen oder eine Phenylgruppe und einer der Reste X ein Halogenatom und der andere Rest X ein Wasserstoff- oder Halogenatom ist.
Die Halogenatome können Fluor-, Chlor-, Brom- oder Jodatome sein. Spezielle Beispiele für die Organozinnverbindungen der allgemeinen Formel I sind Tri-n-butyl- (2-cyan-4-chlorphenoxy)-zinn,
EMI1.2
Tri-n-butyl- (2-cyan-4, 6-dichlorphenoxy)-zinn, Tri-n-phenoxy)-zinn.
Das erfindungsgemässe Verfahren besteht darin, dass man entweder ein Phenol der allgemeinen Formel
EMI1.3
worin X die obige Bedeutung hat, mit einer Zinnverbindung der allgemeinen Formel Y-Sn (R) g. (III) worin R die obige Bedeutung hat und Y ein Chloratom oder eine Hydroxylgruppe ist, oder ein Alkalimetallsalz des Phenols der allgemeinen Formel II mit der Zinnverbindung der allgemeinen Formel III, worin Y ein Chloratom ist, kondensiert.
Vorzugsweise wird die Umsetzung in einem geeigneten Lösungsmittel, z. B. einem Kohlenwasserstoff oder Keton, durchgeführt.
Die Organozinnverbindungen der allgemeinen Formel I sind wertvolle Biocide mit fungiciden und
<Desc/Clms Page number 2>
insekticiden Eigenschaften, sowie selektive Herbicide. Sie können zur Verhinderung oder Hemmung des Wachstums von verschiedenen Pilzen, Pflanzen, Insekten oder andern Schädlingen verwendet werden.
Besonders wertvoll sind die Organozinnverbindungen der allgemeinen Formel I als Fungicide. Insbesondere werden die neuen Verbindungen verschiedenen Beschichtungsmassen sowohl auf Lösungsmittelbasis als auch auf Wasserbasis einverleibt, um sie gegen Pilzbefall zu schützen. Besonders wertvoll sind die erfindungsgemäss hergestellten Organozinnverbindungen in Beschichtungsmassen, die als Bindemittel entweder ein Ölharz oder ein wasserunlösliches Polymerisat enthalten.
Die neuen Organozinnverbindungen können ferner auf verschiedene Pflanzen und tierische Schädlinge aufgebracht werden, um sie zu bekämpfen und abzutöten. Die erfindungsgemäss hergestellten Organozinnverbindungen sind zwar wirksame Biocide, ihre maximale biocide Wirkung hängt jedoch von der Art der Substituenten am Benzolkem und am Zinnatom ab.
Zur Bekämpfung von Schädlingen können die Organozinnverbindungen entweder auf den Ort aufgebracht werden, der von Schädlingsbefall geschützt werden soll, oder die Verbindungen können unmittet- bar auf die Organismen aufgebracht werden, deren Wachstum bekämpft oder unterdrückt werden soll. Die Organozinnverbindungen können als solche zur Bekämpfung von unerwünschten Organismen angewendet werden. Meist und vorzugsweise werden sie jedoch zusammen mit einem inerten Träger eingesetzt, der die Anwendung dosierter Mengen der Organozinnverbindungen erleichtert und die Aufnahme durch die Organismen fördert, deren Wachstum gehemmt werden soll.
Die Organozinnverbindungen können mit feinteiligen, inerten, festen Trägerstoffen, oder in Form von Lösungen oder Dispersionen in inerten organischen Lösungsmitteln, Wasser oder Gemischen inerter organischer Lösungsmittel mit Wasser oder als Öl-in-Wasser-Emulsionen eingesetzt werden.
Das folgende Beispiel erläutert die Erfindung, ohne sie einzuschränken.
EMI2.1
setzt. Die erhaltene Lösung wird bei 25 bis 300C langsam mit 32, 4 g (0, 1 Mol) Tri-n-butylzinnchlorid versetzt. Das Reaktionsgemisch wird 2 h lang unter Rückfluss erhitzt, danach abkühlen gelassen und filtriert. Filtrat wird zur Trockne eingedampft und der Rückstand in 300 ml Benzol aufgenommen. Die Benzollösung wird dreimal mit jeweils 150 ml Wasser gewaschen und anschliessend unter vermindertem Druck eingedampft. Es werden 45,7 g (95, 8% derTheorie) Tri-n-butyl-2- (2-cyan-4, 6-dichlorphenoxy)- zinn als gelbe kristalline Masse erhalten. Das Produkt enthält 15, 78% Chlor und 24, 37% Zinn. Der theo- retische Gehalt an Chlor bzw.
Zinn beträgt 14,87 bzw. 24, 9%.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of new organotin compounds
The invention relates to a process for the preparation of new organotin compounds of the general formula
EMI1.1
in which pure alkyl radical with 4 to 8 carbon atoms or a phenyl group and one of the radicals X is a halogen atom and the other radical X is a hydrogen or halogen atom.
The halogen atoms can be fluorine, chlorine, bromine or iodine atoms. Specific examples of the organotin compounds of the general formula I are tri-n-butyl- (2-cyano-4-chlorophenoxy) tin,
EMI1.2
Tri-n-butyl- (2-cyano-4, 6-dichlorophenoxy) tin, tri-n-phenoxy) tin.
The inventive method consists in that either a phenol of the general formula
EMI1.3
wherein X has the above meaning with a tin compound of the general formula Y-Sn (R) g. (III) where R has the above meaning and Y is a chlorine atom or a hydroxyl group, or an alkali metal salt of the phenol of the general formula II is condensed with the tin compound of the general formula III, in which Y is a chlorine atom.
Preferably the reaction is carried out in a suitable solvent, e.g. B. a hydrocarbon or ketone performed.
The organotin compounds of general formula I are valuable biocides with fungicides and
<Desc / Clms Page number 2>
insecticidal properties, as well as selective herbicides. They can be used to prevent or inhibit the growth of various fungi, plants, insects or other pests.
The organotin compounds of the general formula I are particularly valuable as fungicides. In particular, the new compounds are incorporated into various coating compositions, both solvent-based and water-based, in order to protect them against fungal attack. The organotin compounds prepared according to the invention are particularly valuable in coating compositions which contain either an oleoresin or a water-insoluble polymer as a binder.
The new organotin compounds can also be applied to various plants and animal pests to control and kill them. The organotin compounds prepared according to the invention are effective biocides, but their maximum biocidal effect depends on the nature of the substituents on the benzene nucleus and on the tin atom.
To control pests, the organotin compounds can either be applied to the site which is to be protected from pest infestation, or the compounds can be applied directly to the organisms whose growth is to be controlled or suppressed. The organotin compounds can be used as such for combating undesirable organisms. Mostly and preferably, however, they are used together with an inert carrier which facilitates the use of metered amounts of the organotin compounds and promotes uptake by the organisms whose growth is to be inhibited.
The organotin compounds can be used with finely divided, inert, solid carriers, or in the form of solutions or dispersions in inert organic solvents, water or mixtures of inert organic solvents with water or as oil-in-water emulsions.
The following example explains the invention without restricting it.
EMI2.1
puts. The resulting solution is slowly mixed with 32.4 g (0.1 mol) of tri-n-butyltin chloride at 25 to 30 ° C. The reaction mixture is refluxed for 2 hours, then allowed to cool and filtered. The filtrate is evaporated to dryness and the residue is taken up in 300 ml of benzene. The benzene solution is washed three times with 150 ml of water each time and then evaporated under reduced pressure. 45.7 g (95.8% of theory) of tri-n-butyl-2- (2-cyano-4, 6-dichlorophenoxy) tin are obtained as a yellow crystalline mass. The product contains 15.78% chlorine and 24.37% tin. The theoretical content of chlorine or
Tin is 14.87 and 24.9%, respectively.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT1043470A AT299244B (en) | 1970-11-19 | 1970-11-19 | Process for the production of new organotin compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT1043470A AT299244B (en) | 1970-11-19 | 1970-11-19 | Process for the production of new organotin compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
AT299244B true AT299244B (en) | 1972-06-12 |
Family
ID=3622318
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT1043470A AT299244B (en) | 1970-11-19 | 1970-11-19 | Process for the production of new organotin compounds |
Country Status (1)
Country | Link |
---|---|
AT (1) | AT299244B (en) |
-
1970
- 1970-11-19 AT AT1043470A patent/AT299244B/en not_active IP Right Cessation
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ELJ | Ceased due to non-payment of the annual fee |